An older adult walks out of their room wearing something unexpected: a striped jacket, a colorful scarf, bold glasses, a beautiful, oversized brooch, or a bright orange Tigers T-shirt and vintage cap.

The reaction is almost immediate. “Ooooh, So cute!”

There’s a look of affectionate surprise, as though this person has delighted us simply by stepping outside our expectations.

The intention is usually kindness. But I wonder if, sometimes, we become so busy appreciating the charm that we forget to appreciate the person. Sometimes I’m the first to comment on how wonderful someone looks. And lately, I’ve been thinking about that.

This lesson follows me home. Every now and then my husband comes downstairs after choosing an outfit to wear to dinner out, dressed in one of his favorite well-worn plaid shorts, and I bite my tongue. I may have other fashion ideas, but he’s comfortable, completely content, and, truth be told, he’s handsome enough to make my opinion largely irrelevant.

At Jewish Senior Life, I am surrounded by residents whose clothing tells us a story. Their style is not about looking younger or pretending to be someone else. These are not costumes. They are expressions of identity.

Whether it’s a vintage blazer, dramatic sunglasses, treasured jewelry, flowing silk trousers, bold lipstick, brightly painted summer toes, or a favorite hat worn indoors simply because it brings joy, every choice reflects their history.

Yet too often, the conversation stops at the surface.

We might say: “I love your jacket,” or “What a beautiful brooch.”

But what if we kept going?

Where did you find it? Who gave it to you? What makes it special?

The clothing may begin the conversation, but it should never end there.

It reminds me of a phrase many of us have heard and perhaps even said, “You should dress your age. Who decided that? When did growing older become a reason to become less visible, less playful, or less creative? “Dressing your age” has very little to do with clothing. It’s really a request not to challenge society’s expectations.

A few years ago, Jewish Senior Life hosted JSL Lives Well Lived, a fashion show at The J that showcased our remarkable residents. Inspired by style icons such as Iris Apfel, Diane Keaton, and Debra Rappaport, residents modeled clothing from our campus boutiques in Meer and Fleischman while adding items of their own favorite accessories, chosen simply because they made them feel wonderful.

As they walked onto the runway together, the room filled with applause, laughter, and joy. But I also heard other comments.

“Too much leg.” “Too much makeup. “Trying too hard.” “She shouldn’t wear that.”

The words of self-appointed fashion critics made me think. When did aging become a performance open to public critique? We encourage people to experiment, discover their style, and express who they are. We celebrate originality and confidence. Why should that end as we age?

One of the gifts of growing older should be the freedom to stop living for other people’s approval.

And one of the greatest gifts we can offer people isn’t admiration from a distance or an unsolicited opinion. It’s friendly curiosity.

When you visit Jewish Senior Life and meet the residents ask about the jacket and the brooch. Then ask what they’re reading.

Ask what excites them. Ask what they’ve learned that still guides them today.

And be prepared to listen. Because every older adult is more than what we notice at first glance. They’re not a charming exception to our expectations. They’re a whole life still unfolding.

A person’s appearance may catch your eye, but it’s never the point. The point is recognizing the person who chose what they wanted to wear. Respect is not giving someone permission to be themselves. Respect is understanding they never needed our permission in the first place.

At JSL, we encourage people to express themselves (of course within reason). Vintage Hawaiian shirts and khaki pocket shorts, white socks to the knee with brown shoes… bold colors, oversized blouses, Batman T-shirts with a funny phrase, dramatic reading glasses, bright lipstick, or their favorite straw hat, worn indoors. Let them surprise you.

Often, we discover that the most interesting thing about what anyone is wearing is the remarkable story of the person wearing the clothes.

May we be blessed with curious hearts, generous spirits, and the wisdom to see beyond appearance to the inherent dignity and unique story within each person.

Shabbat Shalom